From Billy Bishop to the Big Leagues: Porter Celebrates 20 Years of Shaking Up Canadian Aviation

“We took a big leap coming out. People have embraced that and we have to celebrate it.”

That leap, as Porter Airlines’ President Kevin Jackson called it, was taken on October 23, 2006, when Porter launched its inaugural flight from Toronto’s Billy Bishop airport (YTZ) into Ottawa, ON.

Now, 20 years later, the airline celebrated its milestone anniversary Thursday night (Oct. 22) with a party in downtown Toronto, at The Radisson Blu, a hotel not far from where that initial flight departed.

“And as we stand here today, we are so substantially larger,” Jackson said at last night’s bash, which Travel Market Report Canada attended. “It’s a very different airline.”

Porter launched with what Jackson called a mission “to redefine what people expected from air travel.”

“It was everything from the way we looked as a carrier to the retro uniforms. It was the onboard service, it was the complimentary beer and wine….and today, we’re still on that mission, redefining what people expect of air travel. Especially within the realm of economy air travel.” he said.

Edmond Eldebs, Porter’s senior vice president and chief commercial officer, elaborated.

“People underestimate how much travellers want a better experience,” he said. “We’ve spent two decades on the little things that make flying something people look forward to.”

Central to Porter’s elevated flying experience are its 132-seat Embraer E195-E2 jets and 78-seat De Havilland Dash 8-400 turboprops, both offering the comfort of no middle seats.

All passengers enjoy complimentary, premium snacks, beer and wine (served in glassware), while those travelling aboard the E195-E2 also benefit from free Wi-Fi.

Eldebs emphasized that Porter’s commitment to elevated service has been a defining feature of the airline since day one, and remains central to its identity today.

“We’re setting a new standard in economy travel and we’re elevating the entire industry with us,” he said.

For Eldebs, Porter’s 20th is a professional and personal celebration. “I’m one of the fortunate few that has been around since the very beginning. It’s quite a big milestone for us,” he said.

Fuel prices “the largest” challenge in Porter’s history

The anniversary party was a moment of celebration, but also a moment of reflection, looking back at a journey that hasn’t been without its fair share of turbulence.

“There has certainly been no shortage of challenges since the very beginning,” said Eldebs. “When we started operating from Billy Bishop, there was quite a bit of challenge around the tunnel being built. Then we were growing in the middle of the 2008 financial crisis. There’s the pandemic, the geopolitical and U.S. tariff situation last year, and of course, right now, we’re in the middle of a fuel crisis.”

On the topic of rising fuel prices, Jackson said: “It certainly is an issue that’s affecting the entire industry.”

“As a business, it’s a challenge for sure. The industry is seeing fares rise, and we’re certainly not passing on all the costs, but it remains a challenge.”

“If I look at the three biggest challenges Porter’s has had in its history: number one is COVID, tariffs are number two, [and] I’m now going to say fuel prices is the largest.”

But like other challenges before it, Porter is confident the storm will be weathered thanks, in part, to the help of industry partners.

“It’s critical. Those are the people behind our success. We cannot be here today without travel agents, customers, our crew members,” said Jackson.

Eldebs added to that notion. “Travel advisors are very important to Porter’s success. They have played a key role in the successful growth we’ve had today,” he said. “We want to make it easy for all advisors to do business with Porter, and we continue to make significant investments there.”

While Porter has expanded significantly since that inaugural Toronto to Ottawa flight 20 years ago, the airline said additional growth is still on the horizon.

“To give you a sense of what’s supposed to come, we have 85 aircraft with an order of up to 140. That should give you a sense of the growth that is yet to come,” said Jackson.

Eldebs added: “We’re in the middle of a significant growth plan and transformation.”

 “I think if I could rewind back to my first day at Billy Bishop, would I have thought we’d be here today? No. So we’ll see what 20 years will bring,” he said.

From Billy Bishop to Canada’s third-largest airline

The anniversary celebrations continued Friday morning (Oct. 23) at Billy Bishop airport.

In a press release issued to coincide with the milestone, Porter highlighted the scale of its transformation from a regional carrier serving Eastern Canada and select U.S. destinations into a growing North American airline with transcontinental service and an expanding network of sun destinations.

Since launching operations, Porter has carried more than 49 million passengers and flown more than 784 million kilometres.

Much of that growth has occurred over the past three years. In 2023, Porter began expanding beyond its regional roots with the introduction of Embraer E195-E2 aircraft, allowing the airline to establish a transcontinental network.

Today, its fleet consists of 56 Embraer E195-E2 jets and 29 De Havilland Dash 8-400 turboprops. The airline currently serves 33 destinations across 131 routes, reaching every Canadian province, the United States, Mexico, the Caribbean and Central America.

While Billy Bishop remains an important part of Porter’s operations, the airline has expanded its presence at Toronto Pearson, Hamilton, London, Ottawa, Montreal and Halifax, offering passengers additional departure options closer to home.

Its network is further supported by airline partnerships, including a joint venture with Air Transat, which allows passengers to connect to destinations beyond Porter’s own routes.

“We set out to redefine economy travel”

Porter CEO Michael Deluce (in Ottawa today for a separate event) reflected on the airline’s evolution and its impact on Canadian aviation.

“From the beginning, we set out to redefine economy travel and make flying something to look forward to. Every product and service detail is intentional—built around warm hospitality, elevated comfort, and appreciation for our passengers,” said Deluce in a statement Monday.

“Two decades later, that relentless commitment has driven our evolution into Canada’s third-largest airline, while introducing sustained competition and establishing service standards not seen in years. None of this growth would be possible without our extraordinary team members. Their passion, resilience, and dedication can’t be matched. As we look to the future, we will continue building an airline that Canadians are proud to fly.”

Over the years, Porter’s service approach has earned international recognition, including being named among the Top 10 International Airlines by Travel + Leisure and Condé Nast Traveller, Best Regional Airline in North America by Skytrax, and Best Economy Class in the USA Today Readers’ Choice Awards.

Birthday giveaways & celebrations in the sky

To mark its 20th year, Porter has introduced a limited-edition merchandise collection, including miniature collectibles known as The Little Things Blind Boxes, a Cabin Crewneck created in collaboration with Kuwalla Tee, a Mr. Porter raccoon plush toy, an Embraer E195-E2 model aircraft and a commemorative baseball cap.

The collection is available exclusively through porter20.com while supplies last.

The airline is also celebrating with its nearly four million VIPorter loyalty members through a special giveaway running from October 15 to November 3.

Under the promotion, one member will receive 20,000 VIPorter points each day for 20 days. Canadian members who have flown with Porter or redeemed points between October 1, 2025, and November 2, 2026, are automatically entered.

Birthday festivities have also taken place throughout the week for employees and passengers at airports across Porter’s network.

Among the highlights was a special flight between Montreal Metropolitan Airport (MET), where Porter launched in June, and Vancouver International Airport (YVR), where passengers were treated to a birthday celebration in the sky, complete with decorations, loot bags and cake.